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DnD 5e - The Rogue Handbook

Last Updated: December 3rd, 2019

Disclaimer

I will use the color coding scheme which has become common among Pathfinder build handbooks, which is simple to understand and easy to read at a glance.

  • Red: Bad, useless options, or options which are extremely situational.
  • Orange: OK options, or useful options that only apply in rare circumstances
  • Green: Good options.
  • Blue: Fantastic options, often essential to the function of your character.

I will not include 3rd-party content, including content from DMs Guild, even if it is my own, because I can't assume that your game will allow 3rd-party content or homebrew. I also won't cover Unearthed Arcana content because it's not finalized, and I can't guarantee that it will be available to you in your games.

Introduction

Rogues are the quintessential Face, Scout and Striker. Sneak Attack allows them to do a huge pile of damage in a single attack, and their pile of skills allows them to easily handle locks, traps, guards, and many other challenges. While a party can function just fine without a Rogue, it's hard to compete with the sheer number of important skill and tool proficiencies offered by the Rogue.

Rogues split into melee or ranged builds. Melee Rogues frequently go for two-weapon fighting because it provides a second chance to score Sneak Attack, and hit-and-run tactics are great way to get into melee to attack before retreating behind your party. Ranged rogues (archer Rogues) typically rely on sniping. Hiding after each attack using Cunning Action is reliable and effective, though it can be very static and repetitive. Arcane Tricksters expand on these options with magic, but when it's time to kill stuff even tricksters use the same tactics.

Rogue Class Features

Hit Points: 1d8 hit points is dangerous if you go into melee alone, so be sure to have a nice tanky ally nearby and a healer waiting in the wings.

Saves: Dexterity saves will protect you from things like fireballs, and Intelligence saves also exist I suppose. Evasion further improves your Dexterity saves.

Proficiencies: Rogues get all of the weapons they need to get by, but thieves' tools, and a fantastic four skills.

Expertise: Rogues are truly the master of skills. Pick skills which fit the theme and style of your campaign and your character well.

Sneak Attack: Sneak Attack is the source of most of the Rogue's damage, and should define your combat tactics. You can only use it once per turn, which is disappointing for two-weapon fighting builds, but once per turn is plenty. Also note that it's per turn, not per round, so you can potentially use your reaction to Sneak Attack a second time in a round.

Thieves' Cant: Really only matters for flavor.

Cunning Action: This is a fantastic option for bringing your Sneak Attack into play. Archers can use Hide to stay hidden between attacks, and melee Rogues can use Dash and Disengage to move around the battlefield safely and quickly.

Roguish Archetype: See "Subclasses - Roguish Archetypes", below.

Uncanny Dodge: If you only draw a handful of attacks this can prevent a huge amount of damage.

Evasion: Between this and uncanny dodge you are very durable.

Reliable Talent: This is especially nice for your Expertise skills, and it's great motivation to pick up the Skilled feat.

Blindsense: Locating invisible creatures can be very hard, and even if you can't hit them easily it goes a long way to know where they are standing.

Slippery Mind: Your Wisdom probably isn 't great, but at this level your Proficiency Bonus is bug enough that this goes a long way.

Elusive: Between this, Uncanny Dodge, and Evasion you are very difficult to kill.

Stroke of Luck: Essential when the chips are down and you can't afford to fail.

Subclasses - Rogue Archetypes

Arcane TricksterPHB

The Arcane Trickster brings magic to the Rogue. Enchantment and Illusion spells both offer fantastic options, trading in utility and trickery for the offensive options of the Assassin or the skill options of the Thief.

  • Spellcasting: The Arcane Tricksters defining feature. You're limited almost exclusively to Enchantment and Illusion spells, but both of those schools work very well for Arcane Tricksters. When selecting spells, remember that Sneak Attack requires Dexterity-base weapon attacks, so you can't apply it to your spells.
  • Mage Hand Legerdemain: Controlling the hand as a bonus action means that you can pick locks and pick pockets while you're doing other things fighting or casting other spells.
  • Magical Ambush: Since your spell DC likely won't be as good as that of a dedicated spellcaster this can really do a lot to improve the reliability of your spells.
  • Versatile Trickster: Advantage allows you to Sneak Attack the target. Remember that you will need to move the hand into range for this to work, but you can use your Cunning Action on the previous round to do so thanks to Legerdemain.
  • Spell Thief: The obvious use it to steal spells from enemy spellcasters, but in a game when you might go several levels without seeing a spellcaster, a better option is to "steal" spells from your party's other spellcasters. Have them cast a useful low-level spell on you, like a buff spell or polymorph, and cast it on your own without needing to consume other spellcasters precious spell slots.

AssassinPHB

Assassins are good at two things: Infiltration and (you guessed it) assassination. If you want to get into places unsuspected or just straight up murder people, the Assassin is the way to go. However, they lack utility options for handling situations outside their specialized skillset.

  • Bonus Proficiencies: Both tool kits are fantastic and open up wonderful options for the Rogue.
  • Assassinate: This is excellent motivation to lead off every combat with a huge damage die, but Sneak Attack requires that your attack be dexterity-based, so you may want to use a Rapier or Heavy Crossbow (which requires you to find the proficiency somewhere) to deal as much damage as possible.
  • Infiltration Expertise: Situational, but very flavorful, and absolutely fantastic in some situations.
  • Impostor: Situational, but very flavorful.
  • Death Strike: Combined with Sneak Attack and Assassinate, this is an absolutely huge pile of damage.

InquisitiveXGtE

If you want to be really good at Insight and Perception, this is the way to do it. Combined with Expertise there's no one who could reasonably compete with the Inquisitive's powers of perception. However, the archetype offers nothing to do once you notice stuff. It would be great in a campaign that includes lots of traps, hidden doors, and people who lie to you, but in situations not specifically tailored to the Inquisitive's skillset they fall back on basic Rogue class features.

  • Ear for Deceit: This makes Insight much more reliable. In a small party where you can't hope for a good role due to sheer numbers, this is wonderful.
  • Eye for Detail: Finding hidden creatures normally requires an action to attempt, which is a serious problem if you're ever attacked by stealth enemies which like to hide and snipe at you from afar.
  • Insightful Fighting: Ear for Deceit will make this very reliable, and it last for a full minute so you have plenty of time to benefit. Even if you lose the opposed check, you can try again the following round.
  • Steady Eye: Combined with Eye for Detail you're extremely reliable at spotting traps and hidden enemies, but the limitation on movement might be a problem in combat.
  • Unerring Eye: Wisdom isn't an especially useful ability score for rogues, so it's frustrating that this ability is Wisdom-based. However, the effect is extremely useful, so it's hard to complain too much.
  • Eye for Weakness: Extra damage never hurts, but it's not very exciting.

MastermindSCAG / XGtE

The Mastermind works best in a game with a lot of intrigue and social interactions. Half of the abilities won't ever come into play in your typical dungeon-crawl.

  • Master of Intrigue: A pile of proficencies which you might never use, but they might be very useful depending on the style of your game.
  • Master of Tactics: Help gives the target Advantage, which is pretty great for a lot of characters. Of course, as a Rogue no one needs Advantage as much as you. Using this as a bonus action prevents you from using Cunning Action or two-weapon fighting, so your bonus actions will always be a very difficult trade-off. A good use case would be to use Master of Tactics to give your party's Fighter-equivalent Advantage, then ask them to Shove a target prone so that you can get Advantage on subsequent turns.
  • Insightful Manipulator: A fun way to metagame, but not always useful since in most games you typically won't get to spend a minute chatting up enemeies before weapons come out.
  • Misdirection: Lightfoot Halflings have the ability to hide behind creatures one size larger than they are, which will often also give you cover. It can be a bit rude to shuffle attacks onto an ally, but if you're using a well-armored ally as cover sometimes your ally may be better suited to absorb the attack.
  • Soul of Deceit: Very situational.

ScoutXGtE

Scouts easily outcompete Rangers in skill use with Nature and Survival, but lack any of the actual Ranger flavor. If you want to play a Rogue in a wilderness game, you could definitely do worse, and it's hard to think of a better way to make a Rogue that uses a bow. The Scout manages to keep you at a nice safe distance, keeping you safely out of attack range while your allies distract enemies long enough for you to Sneak Attack them.

  • Skirmisher: Potentially fantastic, but if the attacker has more movement they may be able to follow you. Try to force them to run past someone in your party who can make a decent Opportunity Attack. On your own turn, try to stay as far away from enemies as possible while still being able to Sneak Attack so that they can't outrun you.
  • Survivalist: Two new skills and Expertise in both of them.
  • Superior Mobility: Really helpful in conjunction with Skirmisher and your need to stay as far away as you can.
  • Ambush Master: Plan to pick up the Alert feat for the bonus to Initiative rolls. You want to go firs to maximize the utility of this ability. Encourage your allies to focus on your target and quickly eliminate high-priority targets early in the fight before worrying about other enemies.
  • Sudden Strike: This extra attack consumes your bonus action, so two-weapon fighting is redundant. Allowing you to Sneak Attack twice in a turn effectively doubles your damage output, which is amazing at any level.

SwashbucklerSCAG / XGtE

The Rogue's biggest challenge is applying Sneak Attack reliably. While that's relatively easy in 5e, there are still times when you won't manage to Sneak Attack. The Swashbuckler all but eliminates these times, making the Rogue an even more reliable source of damage. In addition, the Swashbuckler has fantastic abilities for moving through combat, evading enemies, and even forcing them to engage the Swashbuckler, thereby allowing the Rogue to serve as the party's Defender.

  • Fancy Footwork: You only need to attack the target, not hit them, so if you miss and don't want to stay in melee range you're free to retreat unimpeded. Using two light-weapons for two-weapon fighting allows you to move past two enemies if you feel the need. The choice between using Cunning Action to Disengage and relying on Fancy Footwork will depend both on what you're wielding and on how many enemies you need to evade.
  • Rakish Audacity: This is absurdly good. Any Rogue can Sneak Attack if an ally is within 5 feet of the target. Rakish Audacity allows you to Sneak Attack if no one except the target is adjacent to you, which means that as long as you're not getting ganged up on you can reliably Sneak Attack whenever you hit. What's better is that this ability doesn't specify melee attacks, so as long as you can get away from enemies (such as by using Cunning Action to Disengage) you're guranteed to be able to Sneak Attack. Oh, and as if this wasn't absurdly good already, you add your Charisma bonus to Initiative checks on top of your Dexterity.
  • Panache: Tanking generally isn't in the Rogue's skillset, but the first portion of this ability is essentially a taunt. The DM could technically end the ability by having the creature walk out of the 60 foot range, then return, but that would be a cheap metagame trick, so feel free to shame your DM if they try it. If you have enough AC to be a tank (not hard with decent dexterity and possibly a shield). Out of combat, you can use this to Charm creatures, making them a very loyal friend for a very brief period.
  • Elegant Maneuver: Advantage is great, especially on a skill like Athletics which is used to Shove enemies prone. Unfortunately, this uses your Bonus Action just to grant you the bonus, so you still need to use your Action to use the skill, leaving you no opportunity to attack. This won't combine with Shield Master's ability to Shove as a Bonus Action.
  • Master Duelist: Sometimes you can't risk missing, and in those cases this is a life saver. Most of the time you can still use Fancy Footwork to move away and return to attack later, but sometimes that just isn't an option.

ThiefPHB

The Thief is the vanilla Rogue, but that is not to say that it's boring. A Thief is reliable and very effective at the tasks which you most associate with Rogues.

  • Fast Hands: Disarming traps and open locks can typically wait until you finish combat, but using an option as a bonus action can include cool things like drinking potions.
  • Second-Story Work: Situational.
  • Supreme Sneak: If you combine this with Expertise, you are as close to undetectable as you can get without being magically silenced and invisible.
  • Use Magic Device: This opens up all manner of weapons, wands, and staves which are normally limited to specific characters.
  • Thief's Reflexes: Two entire turns is crazy. You can Sneak Attack twice, possible before enemies get a chance to act.

Abilities

Dexterity is key for any Rogue, and Intelligence is important for Arcane Tricksters, but your Wisdom and Charisma depend largely on your choice of skills and role in the party.

Str: Dump stat. Nothing that the Rogue does uses Strength.

Dex: Rogues run on Dexterity. They add to you skills, your tools, your attacks, your damage, your AC, and your best save.

Con: Hit points are always important, especially for melee Rogues.

Int: Arcane Tricksters need Intelligence for their spells, but other Rogues only need it for Investigation.

Wis: Helpful for Insight Perception, but otherwise useless. Inquisitives will want a bit more to power Unerring Eye.

Cha: Rogues make a great Face, and you can't be a Face without Charisma.

Most Rogues Arcane Trickster
Point Buy Standard Array Point Buy Standard Array
  • Str: 8
  • Dex: 15
  • Con: 14
  • Int: 11
  • Wis: 12
  • Cha: 12
  • Str: 8
  • Dex: 15
  • Con: 14
  • Int: 10
  • Wis: 13
  • Cha: 12
  • Str: 10
  • Dex: 15
  • Con: 14
  • Int: 14
  • Wis: 10
  • Cha: 10
  • Str: 8
  • Dex: 15
  • Con: 13
  • Int: 14
  • Wis: 12
  • Cha: 10

Races

Dexterity bonuses are critical, and Darkvision is fantastic for sneaking around in the dark. Size doesn't matter sinc Rogues don't use heavy weapons.

AarakocraEEPC: Fantastic for an archer Rogue. Flying makes getting places much easier, especially where things like walls are an issue, and it keeps you out of range of enemies. Bonus Dexterity is also nice.

AasimarVGTM:

  • Fallen: Nothing useful for the Rogue.
  • Protector: Nothing useful for the Rogue.
  • Scourge: Nothing useful for the Rogue.

BugbearVGTM: The Strength increase is totally wasted on a rogue, but reach is hard for rogues to get, you get Stealth proficiency for free, and Surprise Attack stacks with Sneak Attack so you can deal 3d6+weapon damage at first level and one-shot many enemies.

Dwarf: The Dwarf's abilities are tangentially helpful for the Rogue, but they have trouble competing with races which provide a Dexterity bonus. Darkvision is particularly helpful.

  • DuergarSCAG: Slightly better for Rogues the Mountain Dwarf, especially in a subterranean campaigns, if only because of Invisibility. Of course, Arcane Tricksters can cast that on their own, so it's not all that great.
  • HillPHB: Extra hit points are nice, and a bit of Wisdom helps with Perception, but it's not very exciting.
  • MountainPHB: Strength and medium armor are both useless for Rogues.

DragonbornPHB: Nothing useful for the Rogue.

ElfPHB: A bonus to Dexterity and Darkvision are perfect for a Rogue.

  • Drow: Improved Darkvision range is helpful for ambushing enemies which also have Darkvision, but the limitation in direct sunlight is really impractical in games which aren't subterranean.
  • EladrinMToF: On par with the High Elf, Fey Step is a massive benefit for a class so dependent on stealth and surprise, and occasionally on running when a fight turns sour. While the High Elf is better for Arcane Tricksters, the Eladrin is great for other builds, especially if you're playing the party's Face.
  • High Elf: An Intelligence boost is good for Arcane Tricksters, but any archer Rogue will enjoy proficiency with Longbows, and a free cantrip offers some interesting options (Green-Flame Blade is a go-to options for the easy damage boost).
  • Sea ElfMToF: Potentially useful in an aquatic campaign, but otherwise nothing special.
  • Shadar-KaiMToF: If you're not going for Arcane Trickster and you still want teleportation, the Shadar-Kai is a better option than the Eladrin.
  • Wood Elf: Wisdom is great for Perception, and any archer Rogue will enjoy proficiency with Longbows. Mask of the Wild is situational, but it offers some helpful options for stealth.

FirbolgVGTM: Nothing useful for the Rogue.

GenasiEEPC: A Constitution bonus never hurts, but Rogues who take a lot of damage don't live very long no matter how many hit points they have.

  • Air: The Dexterity bonus isn't enough to make up for the Air Genasi's lack of useful special abilities.
  • Earth: Nothing useful for the Rogue.
  • Fire: Decent for an Arcane Trickster since tricksters generally don't get access to direct damage spells.
  • Water: Nothing useful for the Rogue.

Gith: Nothing useful for the Rogue.

  • GithyankiMToF: Nothing useful for the Rogue.
  • GithzeraiMToF: Nothing useful for the Rogue.

Gnome: Intelligence and Darkvision work for an Arcane Trickster, but other Rogues won't get as much benefit from Intelligence.

  • Deep (Svirfneblin)EEPC / SCAG: Fantastic in a subterranean game.
  • ForestPHB: Dexterity is great for a Rogue, and combined with the base Gnome's Intelligence bonus this is a fantastic choice for an Arcane Trickster.
  • RockPHB: The Constitution buff is the only thing with any significant game effect.

GoblinVGTM: The ability scores are fantastic, but Nimble Escape is totally redundant with Cunning Action.

GoliathEEPC: Goliaths are Strength-based melee monsters, which really don't work for the Rogue.

Half-Elf: Darkvision, two free skills and some really great ability buffs. Great for any Rogue, but especially good if you plan to play a Face.

  • AquaticSCAG: Only if you're in an aquatic campaign.
  • DrowSCAG: Arcane Tricksters get access to similar options.
  • High/Moon/SunSCAG: A single cantrip gets you access to either Green Flame Blade or Thundering Blade, both of which are fantastic damage boosts for melee Rogues.
  • Keen SensesSCAG: The sidebar describing half-elf variants specifices that you can take Keen Senses in place of Skill Versatility, or a trait based on your elf parentage. Keen Senses give you a single fixed skill, and you're giving up proficiency in any two skills. It should be immediately apparent that this is a terrible trade.
  • WoodSCAG: Mask of the Wild is tempting, and Fleet of Foot is great for hit-and-run tactics, but there are better options.
  • VanillaPHB: Rogues get a lot of skills, but not nearly enough to cover everything that a Rogue should do, especially if you're the party's Face.

Half-OrcPHB: I really want to use Savage Attacks with the Assassin's Assassinate ability, but the Half-Orc's ability bonuses just don't help a Rogue.

HalflingPHB: A Dexterity bonus is great, and Lucky is always helpful, especially since Rogues generally only get one or two attacks.

  • GhostwiseSCAG: Silent Speech is a fun trick, but you'll get more mileage out of other halfling subrace traits.
  • LightfootPHB Hide behind the fighter!
  • StoutPHB Good for a durable Rogue, but not as stealthy or charismatic as the Lightfoot Halfling.

HobgoblinVGTM: The ability score increases don't help much, but Saving Face is great on a class which frequently needs to depend on a single attack per round.

HumanPHB: Versatile and fantastic at everything.

  • Vanilla: Rogues have enough skills that they can reasonably justify having several good ability scores, so take advantage of the point buy method and Human's ability modifiers, and boost a bunch of base 13s.
  • Variant: You still get crucial bonuses to Dexterity and something else, and you can get an awesome feat at level 1. The additional skill is also helpful, but between the four skills from being a Rogue and the two from your background, it's hardly necessary.

KenkuVGTM: Good ability score increases and two free skills. Not quite as good as other races but still a good option.

KoboldVGTM: Pack Tactics is insanely powerful for rogues. Get a familiar, a summoned creature, or a friend to stand next to whatever you want to kill and you get automatic Advantage. Sneak Attack is basically guranteed. Oh, and the ability increases are fantastic. I'm still super angry that WotC re-introduced ability score penalties, but I'm sure all of the kobold rogues running around with 6 Strength will get through life just fine.

LizardfolkVGTM: Natural armor will provide more AC than manufactured armor can, and two free skills are a nice complement to the Rogue's already expansive skillset. Lizardfolk do great when built to emphasize Dexterity, but Hungry Jaws is always dependent on Strength, so emphasizing Dexterity may mean giving up on Hungry Jaws.

LocathahLR: The only useful parts are the Dexterity increase and the free skills.

OrcVGTM: Nothing useful for the Rogue.

TabaxiVGTM: Everything about the Tabaxi is perfect for the Rogue. You don't get to select from a list of skills like the Kenku does, but basically every Rogue in existence wants Perception and Stealth anyway.

Tiefling: Darkvision and the free spells offer some interesting options, especially with the numerous Tiefling subraces. Depending on your archetype and whether or not you want to be a Face you'll find some subraces more appealing than others.

  • AsmodeusMToF: The ability scores don't work as well as Feral, but not bad for a Face.
  • BaalzebulMToF: Bad ability spread.
  • DispaterMToF: Good ability spread, and interesting spell options. This is a great option in a campaign with a lot of intrigue, espionage, and social interaction.
  • FiernaMToF: Bad ability spread.
  • GlasyaMToF: Ideal for tiefling rogues. Legacy of Malbolge offers useful spell options normally only available to arcane tricksters.
  • LevistusMToF: Bad ability spread.
  • MammonMToF: Bad ability spread.
  • MephistophelesMToF: Bad ability spread.
  • ZarielMToF: Bad ability spread.
  • Variant: FeralSCAG: Perfect for an Arcane Trickster.
  • Variant: Devil's TongueSCAG: Tempting if you are building a Face with decent Charisma, but better as a Bard.
  • Variant: HellfireSCAG: If you're casting Burning Hands then you're not using Sneak Attack.
  • Variant: WingedSCAG: On a Rogue I would absolutely take flight over the free spells.

TortleTP: Rogues can't make effective use of Strength or Wisdom, and none of the Tortle's other traits are especially appealing.

TritonVGTM: Nothing useful for the Rogue.

VerdanAcInc: The Verdan has a lot that's useful for the Rogue, but without a Dexterity increase you'll have a lot of problems in combat.

Yuan-Ti PurebloodVGTM: Nothing useful for the Rogue.

Setting-specific races are address below. Not every setting allows every race, and while most races presented in the core rules and in content for the Forgotten Realms can be used in other settings, races specific to settings like Ravnica aren't typically allowed in other settings. Talk to your DM about what races are allowed in your game.

Races of Eberron

BugbearERLW: See above.

ChangelingERLW: Changelings make natural rogues. Dexterity, Charisma, extra Face skills, and the ability to change your appearance at will allow the Rogue to conduct all sorts of subterfuge. However, because the Changeling's capabilities are so heavily devoted to social situations, you may have trouble delving dungeons compared to other races.

GoblinERLW: See above.

HobgoblinERLW: See above.

OrcERLW: See above.

KalashtarERLW: Bad ability spread.

ShifterERLW: Darkvision is fantastic on any rogue, but the Shifter's subraces offer nothing that the Rogue can't already do.

  • Beasthide: Bad ability spread.
  • Longtooth: Bad ability spread, and the bonus action bite attack can't deal Sneak Attack.
  • Swiftstride: The ability score increases are great, but the Shifting Feature doesn't give you anything that you couldn't already do with Cunning Action.
  • Wildhunt: The ability increases are fine, but the Shifting Feature is almost useless.

WarforgedERLW: The flexible ability increase can give you the crucial Dexterity increase, but the bonus to AC isn't as important to the Rogue because it's so easy for the Rogue to remove themselves from situations where they would take damage, and you can rely on Uncanny Dodge to mitigate any damage you do suffer. Still, if you want to be a rogue but you also need to be your party's Defender, consider a Swashbuckler build. If you get proficiency with shields, you can manage an AC of 20, and with Uncanny Dodge you'll be difficult to kill despite relatively poor hit points compared to the Fighter.

Dragonmarks

While the design intent for Dragonmarks was that they would offer some innate spellcasting for everyone, every dragonmark includes an expanded spell list which is arguably a more significant benefit than most of the provided racial traits. Because the expanded spell options are such an important part of the dragonmarks, if you're not playing a spellcaster you're giving up a huge part of your racial traits, which makes it exceptionally difficult to justify playing a dragonmark character who can't cast spells.

Dragonmarked DwarfERLW: Dragonmark traits replace your subrace.

  • Mark of Warding: Bad ability spread.

Dragonmarked ElfERLW: Dragonmark traits replace your subrace.

  • Mark of Shadow: An obvious choice for the Rogue. Unfortunately, Mark of Shadow's spell options are almost all available to the Arcane Trickster already, so the only rogue subclass which can use the extra spells gains very little benefit from them.

Dragonmarked GnomeERLW: Dragonmark traits replace your subrace.

  • Mark of Scribing: Bad ability spread.

Dragonmarked Half-ElfERLW: Dragonmark traits replace some of your normal racial traits, as described in the entry for each Dragonmark.

  • Mark of Detection: The flexible ability increase can go into Dexterity, and the spellcasting adds divination options which the Arcane Trickster can't usually cast, allowing you to use magic to improve your scouting abilities.
  • Mark of Storm: The ability increases work for the Rogue, and while the innate spellcasting is underwhelming the expanded spell list adds several excellent utility options for the Arcane Trickster.

Dragonmarked Half-OrcERLW: Dragonmark traits replace ALL of your racial traits.

  • Mark of Finding: Bad ability spread.

Dragonmarked HalflingERLW: Dragonmark traits replace your subrace.

  • Mark of Healing: The ability score increases work fine, and the expanded healing options allow the Arcane Trickster to serve as a healer in a pinch. Rogues tend to stay alive when things go poorly for the rest of the party, so having access to Healing Word is a benefit which is difficult to ignore.
  • Mark of Hospitality: The ability score increases work fine, but the spells aren't especially useful for a class with access to so little spellcasting.

Dragonmarked HumanERLW: Dragonmark traits replace ALL of your racial traits.

  • Mark of Finding: See Mark of Finding under Dragonmarked Half-Orc, above. Mechanically, the final racial traits are identical.
  • Mark of Handling: Thematically a scout rogue makes sense, but to benefit from the spellcasting you want to play an arcane trickster. The ability score increases work fine, and the spells are neat, but I would only consider this if your DM will allow you to tame creatures in a way that goes beyond your class features.
  • Mark of Making: The ability increases work for the Arcane Trickster, but the spellcasting does surpisingly little to help you. Magic Weapon doesn't affect Shadow Blade, which becomes a central part of your combat repertoire. Similarly, Elemental Weapon isn't very useful when you're only making one attack per turn.
  • Mark of Passage: Perfect ability score increases, and the spellcasting adds a ton of useful options for the Arcane Trickster, who typically has very little access to teleportation.
  • Mark of Sentinel: Bad ability spread.

Races of Ravnica

CentaurGGTR: Nothing useful for the Rogue.

GoblinGGTR: See above.

LoxodonGGTR: Nothing useful for the Rogue.

MinotaurGGTR: Nothing useful for the Rogue.

Simic HybridGGTR: Versatile and fantastic.

VedalkenGGTR: Nothing useful for the Rogue.

Skills

  • Acrobatics (Dex): Very situational.
  • Athletics (Str): Rogues don't really do anything that requires Athletics. Thieves might want it for climbing, but even that is very infrequent.
  • Deception (Cha): Important for a Face.
  • Insight (Wis): Important for a Face.
  • Intimidation (Cha): Important for a Face.
  • Investigation (Int): Very helpful, but not as important as Perception.
  • Perception (Wis): Perception is by far the most important skill in the game, and it's important that several characters in the party have it.
  • Performance (Cha): Performance is for Bards.
  • Persuasion (Cha): Essential for a Face.
  • Sleight of Hand (Dex): Sleight of Hand is very thematic for many Rogues, but it's not very useful.
  • Stealth (Dex): A Rogue without Stealth is a very strange Rogue.

Background

This section does not address every published background, as doing so would result in an ever-growing list of options which don't cater to the class. Instead, this section will cover the options which I think work especially well for the class, or which might be tempting but poor choices. Racial feats are discussed in the Races section, above.

Rogues can do a lot, but they also need a lot of skills to do it all. Look for backgrounds which fill in proficiencies which are already on the Rogue skill list but which you couldn't get with yoour choice of two skills.

  • AcolytePHB: Insight and Religion can be decent options for a Rogue with the right abilities, and extra languages are helpful for a Face.
  • CharlatanPHB: Two Rogue skills and two tool kits.
  • City WatchSCAG: Athletics doesn't do much for Rogues, but Insight and free languages are great for a Face.
  • Cloistered ScholarSCAG: Two knowledge skills and two language can be excellent additions to a Face with decent Intelligence.
  • CourtierSCAG: Perfect for a Face.
  • CriminalPHB: Two important Rogue skills, and two tool kits. You already get Thieves' Tools proficiency as a Rogue, so you can replace Thieves' Tools with another proficiency of the same type. I recommend Poisoner's Kit.
  • EntertainerPHB: Disguise Kit proficiency is really the only interesting piece.
  • Faction AgentSCAG: Fantastic for a Face, and it allows you to fill in a social skill which you couldn't get elsewhere.
  • Far TravelerSCAG: Two excellent skills for a Rogue, a bonus language, and proficiency with an item that you'll probably never use.
  • Guild ArtisanPHB: Two important skills for any Face, but the tool proficiency isn't very helpful.
  • InheritorSCAG: You can't really use Survival, but the rest is decent. Far Traveler provides similar options with better skills.
  • Mercenary VeteranSCAG: Athletics is occasionally useful for Rogues, and any face needs Persuasion.
  • NoblePHB: A good choice for a Face. History is decent if you have a bit of Intelligence to back it up.
  • SagePHB: An Arcane Trickster might have enough Intelligence to justify two knowledge skills, and the extra languages are nice for a Face.
  • Urban Bounty HunterSCAG: Basically two additional skill choices from the Rogue class skills, plus some tool proficiencies, including the ever-important Thieve's Tools.
  • UrchinPHB: Two important Rogue skills, and two tool kits. You already get Thieves' Tools proficiency as a Rogue, so you can replace Thieves' Tools with another proficiency of the same type. I recommend Poisoner's Kit.
  • Waterdavian NobleSCAG: Potentially good for a Face with decent Intelligence.

Feats

This section does not address every published feat, as doing so would result in an ever-growing list of options which don't cater to the class. Instead, this section will cover the backgrounds recommended in the "Quick Build" section of the class description, as well as other backgrounds which I think work especially well for the class, or which might be tempting but poor choices. The possibility of custom backgrounds also means that it is literally impossible for me to provide comprehensive analysis of every potential background in existence.

  • AlertPHB: Going first is great for Rogues, especially Assassins.
  • ActorPHB: Complements the Assassin's disguise and infiltration abilities very nicely.
  • Crossbow ExpertPHB: If you're built to fight at range, Crossbow Expert is tempting. Allowing an additional crossbow attack as a bonus action gives you a backup option if you fail to deliver a Sneak Attack on your first attack, and unlike two-weapon fighting you get to apply your ability modifier to damage with the additional attack. However, there are easy ways to avoid needing this even if you plan to fight at range. The "loading" weapon property doesn't require that your hands remain empty for any specific portion of your turn, so you can fire your crossbow, draw a dagger as your free item interaction, throw it as a bonus action using the two-weapon fighting rules, then have a hand free to reload your crossbow. The ability to use ranged weapons while adjacent to enemies is also tempting, but that's what Cunning Action is for.
  • Defensive DuelistPHB: Very tempting for melee Rogues, but Uncanny Dodge also uses your reaction, and fills roughly the same function.
  • Dual WielderPHB: The best case scenario for this feat is upgrading from two short swords to two rapiers, and the tiny bit of extra damage is hardly worth a feat.
  • Dungeon DelverPHB: Handling traps and secret doors frequently falls to the Rogue, and with the Rogue's skills this can make you extremely effective in a dungeon-heavy campaign.
  • DurablePHB: Leave this for your party's front line.
  • Elemental AdeptPHB: Offensive spells aren't a goot option for Arcane Tricksters because you can't apply Sneak Attack.
  • Inspiring LeaderPHB: A Rogue with good enough Charisma to use this feat is an excellent choice. Temporary hit points hugely reduce your need for magical healing, and there is little reason not to use this before every fight.
  • Magic InitiatePHB: The Sword Coast Adventurer's Guide introduced Booming Blade and Green-Flame Blade, both of which are an Action and allow you to make a melee attack with a weapon, thereby allowing you to use them in conjunction with Sneak Attack. Since Rogues never get Extra Attack, these cantrips can be a significant boost to both damage and utility. Booming Blade is a great way to discourage enemies from following you after you hit them and using Cunning Action to Disengage, and Green-Flame Blade grants some easy bonus damage, plus it allows you to damage a second target, which is particularly nice since Rogues are so bad at handling crowds of enemies. You may also consider options like True Strike to get easy advantage (it only has somatic components, so you can easily use it while hiding). Unless you're an Arcane Trickster, the 1st-level spell should probably be a long-duration buff like Mage Armor (don't do it; real armor is better) or a reliable utility option. Find Familiar is tempting so that you can get an owl to fly in and out of combat taking the Help action, but you get to cast the spell daily so you may want something that you'll definitely use on a daily basis so you don't feel like your under-using the feat.
  • Martial AdeptPHB: One maneuver per short rest isn't enough to justify this for the Rogue.
  • MobilePHB: Hit-and-run tactics are great for melee Rogues, but moving out of a creatures threatened area is normally dangerous. This allows you to run in, attack, then run away safely. You can use Cunning Action to Dash, allowing you to move considerably further in one round, and possibly to hide behind difficult terrain.
  • Moderately ArmoredPHB: You need to be improving your Dexterity enough that medium armor shouldn't be a good option.
  • ObservantPHB: Potentially helpful if no one else in your party has Investigation or Perception, but probably overkill. If you really need this, use Expertise to improve your skills.
  • ResilientPHB: Constitution or Charisma saves are both passable options.
  • Ritual CasterPHB: A great way for Arcane Tricksters to improve their utility options if your party lacks dedicated spellcasters. Find Familiar is a fantastic option because your familiar can take the Help action to grant you Advantage on your attacks.
  • Savage AttackerPHB: This is a bad feat. The largest damage die (d12), yields an average of 2 extra damage per turn.
  • SentinelPHB: Sentinel can be a great way to get opportunity attacks, thereby giving you more opportunities to apply Sneak Attack. However, you may find it difficult to apply Sneak Attack because you can't guarantee positioning or Advantage on other creatures' turns. An enemy could easy move around within your reach until it is no longer adjacent to one of your allies before leaving your threatened area, thereby avoiding the bonus damage from Sneak Attack. Swashbucklers will be able to make best use of this part of the feat since their positioning requirements are so easily met. It's also unlikely that enemies will attack your allies while you're in reach because rogues are relatively soft targets. With light armor and 1d8 hit points, you're among the most frail melee characters. However, if you have a paladin in the party you can capitalize on options like Compelled Duel.
  • SharpshooterPHB: Absolutely fantastic for archer Rogues. Combined with Sneak Attack, you can do some truly crazy damage. Just be sure that you have advantage, or you're going to miss frequently.
  • Shield MasterPHB: A Swashbuckler with Expertise in Athletics can make excellent use of the first benefit, and the added bonus to your already excellent Reflex saves will make the third benefit especially potent. However, many Rogues prefer to carry a secondary weapon in their off-hand so that they can get a second chance at Sneak Attack if they miss with their first attack.
  • SkilledPHB: With Reliable Talent you can reliably use any skill you know, even with a mediocre ability score.
  • SkulkerPHB: Very helpful for archer Rogues who like to rely on sniping.
  • Spell SniperPHB: You still can't use Sneak Attack with spells.
  • War CasterPHB: Tempting for Arcane Tricksters, but since you can't sneak attack with a spell you're better off sticking to a weapon.
  • Weapon MasterPHB: You have every weapon you could want except the Heavy Crossbow, and that's not enough to waste a feat.

Weapons

  • Crossbow, Hand: A decent ranged weapon, but it doesn't do anything that you can't do with a light crossbow.
  • Crossbow, Light: The go-to ranged weapon. The same range as a short bow with a better damage die. The reload property doesn't matter since rogues don't get Extra Attack.
  • Dagger: Great for Two-weapon fighting, and you can throw them if you need to, but the Short Sword has a slightly larger damage die.
  • Longsword: I'm not sure why Rogues get proficiency with long swords.
  • Rapier: Your best bet for single-weapon melee.
  • Shortsword: Ideal for Two-weapon fighting. Comparable to daggers, but you can't throw them
  • Short bow: Light crossbow is strictly better.

Armor

  • Leather: Free starting armor for light armor users. Upgrade as soon as you can afford it.
  • Studded Leather: Your permanent armor.

Rogue Spells

This is not a comprehensive guide to every available spell, as that would be an exercise in madness. The following is a brief compilation of the most notable spells available to the class. Spells available via Magic Initiate are also excluded; for suggestions for Magic Initiate, see the "Feats" section, above.

This section applies almost exclusively to Arcane Tricksters. Other rogues who take Magic Initiate may also find this section beneficial. Because Arcane Tricksters are mostly limited to Enchantment and Illusion spells, I'll focus on those spells here, but I will note some notable options for the total of 7 spells which you can learn that go beyond the school limitation.

It may be helpful to see the Spells section of my Wizard Handbook for advice on spells which go beyond this limitation. Also remember that your cantrips are not limited to Enchantment/Illusion.

When selecting spells, remember that your Intelligence is likely much lower than a comparable wizard, and that you can't deal Sneak Attack damage with spell attacks. Try to avoid spell attacks and spells which require a saving throw from targets.

Cantrips

  • Booming Blade: Attack, then use Cunning Action to Withdraw. Instant hit-and-run tactics, and if enemies chase you they take extra damage.
  • Green-Flame Blade: Allows you to attack two enemies at once, which rogues are generally bad at doing.
  • Minor Illusion: Room for plenty of creative, deceptive uses.
  • Sword Burst: If you are in a position where it makes sense to use this, you should be running away.

1st-Level Spells

  • Absorb ElementsPHB: Outside of your school limitations. Uncanny Dodge only applies to attacks, but you can use Absorb Elements to mitigate damage from other sources, dramatically improving your ability to endure damage.
  • Find FamiliarPHB: Outside of your school limitations. An owl can move into melee range, then Dash away using its Flyby ability to avoid provoking Opportunity Attacks. This allows you to easily target foes for Sneak Attack with very little effort on top of the other fantastic benefits of having a familiar. I just wish that the owl wasn't so significantly better than every other option so that there was a good reason to consider other types of familiars.
  • Mage ArmorPHB: Outside of your school limitations. This will raise your maximum AC by 1 compared to Studded Leather.
  • ShieldPHB: Outside of your school limitations. Redundant with Uncanny Dodge.
  • Silent ImagePHB: While not nearly so powerful as Major Imagine, if you just want an object or a visual effect, Silent Image does the job just as well. Throw up a fake wall, door, or portcullis to slow pursuers. Create a piece of furniture, then hide inside it and stab people when they try to open it. Illusions are limited more by your creativity (and your DM's willingness to play along) than by the spell's text.

2nd-Level Spells

  • BlurPHB: A fantastic defensive buff, especially if you're fighting in melee.
  • DarkvisionPHB: Outside of your school limitations. Darkvision is crucial for a class that benefits so much from fighting in the dark, so if you don't have this from your race or from an ally, you should strongly consider it.
  • InvisiblityPHB: Essential.
  • Mirror ImagePHB: As effective as Blur (at least until you take a couple hits), and it doesn't require Concentration.
  • Misty StepPHB: Outside of your school limitations. Fantastic short-range teleportation.
  • Gift of GabAI: Are you playing a silver-tongued rogue, but in real life you're barely able to string two syllables together? Here's your sollution. But be warned: while the spell doesn't allow a saving throw, it only fixes the past 6 seconds.
  • Magic Mouth: Find a way to cast Thaumaturgy to raise your voice's volume, then cast this spell on a piece of paper and scream into it for as long as you are physically capable. Set the trigger to "when the paper is unfolded". Leave the paper for someone to find, or use mage hand to open it at a distance. Instant distraction. The material component is inexpensive by the time you can cast this, and the duration is "until dispelled", so you can carry about a big stack of pre-cast Magic Mouth spells for all sorts of shenanigans.
  • Major ImagePHB: Fantastically versatile, and creatures don't make a saving throw. Instead, they need to know to make an Intelligence (Investigation) check, or they need to physically interact with the illusion. Even then, you can buy yourself a great deal of time while the target tries to figure out your illusion.
  • Phantom SteedPHB: By the time you can cast this, your allies can likely produce much better ways to travel long distances.
  • See InvisiblityPHB: Outside of your school limitations. Rogues don't have any other good options for dealing with invisible foes.
  • Shadow BladeXGtE: Basically a magic rapier that deals psychic damage, which is very rarely resisted. The blade has both finesse and thrown, so it has all the best parts of a dagger with twice the damage of a rapier. You can upcast the spell to increase the damage dice, but you really don't need to. Gauranteed Advantage while attacking a target in dim light or darkness means that you can easily apply Sneak Attack, and compared to your pile of sneak attack dice the extra d8 isn't worth your extremely limited 3rd-level spell slots.

3rd-Level Spells

  • FlyPHB: It's hard to overstate how powerful flight is.
  • Hallucinatory TerrainPHB: Situational.
  • PolymorphPHB: Tempting and potentially very powerful, but you can't use Sneak Attack while polymorphed and you'll deal more dmaage with Sneak Attack and a dagger than you will by turning into a tyranosaurus.
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4th-Level Spells

  • Greater Invisibility: Probably the most important spell that anyone can cast on a rogue.

Multiclassing

  • Barbarian: Reckless Attack is very tempting because it provides a guaranteed means of gaining Advantage and dramatically improves your probability of applying Sneak Attack. However, one a class as frail as the Rogue it's extremely dangerous to grant Advantage against yourself and there are plenty of other ways to gain reliable access to Advantage and Sneak Attack. At level 18 Elusive negates the downside of Reckless Attack, but building a character around one trick which won't work until level 20 almost never pays off since so few campaigns reach high levels.
  • Fighter: Fighting Style goes a very long way for the Rogue if you go for Archery, but Two-Weapon Fighting is a trap. Adding 2-5 damage (depending on your Dexterity) really won't matter compared to your Sneak Attack damage, so stick to Rogue and save your Bonus Action for Cunning Action. Swashbucklers might consider the Fencing style and pick up a shield (and possibly even medium armor) so that they can make best use of Panache. The +2 damage outpaces the 1.75 average Sneak Attack damage you get per Rogue level, so a single level won't cut into your damage output. If you can suffer three levels of Fighter, the Battle Master offer some useful options. Riposte allows you a reliable way to get an extra Sneak Attack per round (remember that Sneak Attack is once per turn), especially for swashbucklers who can apply Sneak Attack easily in melee. Feinting Attack also provides Advantage, allowing for easy Sneak Attack during your turn. However, thse options depend on Superiority dice, so your usage is severely limited.
  • Monk: Way of the Shadow is a massively tempting option for Rogues, but the 3rd-level benefit isn't worth three levels, and the 6th-level benefit costs you too much to obtain.
  • Ranger: 2 levels gets you a Fighting Style and access to Hunter's Mark, which makes Two-Weapon Fighting more viable (though still not necessarily great). Three levels opens up a Ranger achetype, and the Hunter can select Giant Slayer as their 3rd-level ability. Giant Slayer allows you an attack as a reaction, offering a way to get a second Sneak Attack per round every round.
  • Wizard: Two levels to pick up the Bladesinging tradition offers some excellent options for melee Rogues. Bladesong grants a nice AC boost (especially for Arcane Tricksters) and some other great benefits, and access to Wizard spells removes the need for the Magic Initiate feat. Since you have more spell options than Magic Initiate provides, pick up Find Familiar and have your familiar use the Help action to grant you Advantage (and therefore Sneak Attack) on your attacks.

Example Build - Lightfoot Halfling Rogue (Thief)

When your eyes are at the same level as everyone's pockets, it's really hard to resist the urge to pick them.

This is a "Staple Build". This build is simple, and relies on options from the SRD and the Basic Rules wherever possible. If you need a functional build with nothing fancy or complicated, this is a great place to start.

The Lightfoot Halfling Thief is, in my opinion, the most iconic example of the Rogue. My opinion may be biased by my 3rd-edition roots, in which Lidda the Halfling Rogue was the iconic example of the class, but the concept of a halfling sneaking around stealing things dates all the way back to The Hobbit.

With the options available to us in the Basic Rules and the SRD, we'll build our rogue as a combination Face, Scout, and Striker. These are the Rogue's typical roles, and this build can cover all the bases reasonably well at the same time. Our Face and Scout emphasis will be a balance because each will consume our limited choices of skill proficiencies and Expertise. I'll present some suggested options, but I encourage you to customize your build to suit your tastes.

I'll note two DPR entries below: One for a single attack, and one for two-weapon fighting. While the additional attack itself does a miniscule amount of additional damage, the additional opportunity to deal Sneak Attack damage is a massive mathematical advantage that only grows as you gain levels.

Abilities

We will use the ability scores below. They're almost identical to the suggested ability scores presented above for "most rogues", but they're tweaked a little bit to take advantage of the Lightfoot Halfling's ability score increases so that we can get as much out of our build as possible.

Base Increased
Str 8 8
Dex 14 16
Con 14 14
Int 12 12
Wis 12 12
Cha 13 14

Race

Lightfoot Halfling. Dexterity and Charisma is likely the best ability score spread we can get for a thief, and the Lightfoot Halfling's other racial traits offer a bunch of other useful tricks.

Skills and Tools

Rogues get more skills at first level than any other class, and they also get Expertise immediately. You also get Thieves' Tools proficiency on top of the rest.

  • Perception
  • Persuasion
  • Sleight of Hand
  • Stealth

If you choose the Criminal background, you'll get a redundant Stealth proficiency which you can trade for Insight or Intimidation. If you choose the Noble background you'll get a redundant Persuasion proficiency which you can trade for Deception.

For Expertise, I recommend Perception and Stealth. Other skills are appealing, but you're more likely to die because of a failed Perception or Stealth check than for failed Persuasion check. At 6th level you'll get Expertise in two more skills, at which point you should consider skills which fit your campaign. If you're doing a lot of stealing, consider Sleight of Hand and Thieves' Tools. If you're doing a lot socially acceptable things, consider Deception and Persuasion.

Background

Criminal is the obvious choice here, so we'll pick Criminal. However, it might not be the best choice among those available to use. Rogue grants Thieves' Tools proficiency automatically, so Criminal's tool proficiency is redundant. Under the rules for backgrounds, you can replace a redundant proficiency with one of the same type, but what other set of tools do you want? If you want proficiency in something like Healer's Kit or Herbalism Kit, Criminal is great. If you can't think of a second set of tools, look for other background options.

If Criminal doesn't work for you, consider Noble. History proficiency isn't a great choice for our low-Intelligence build, but you get Persuasion, a gaming set, and a language, and Position of Privilege is a great way to roleplay yourself into places with nice things to steal.

Feats

Rogues get one more ability score improvement than most classes, and you only need to bring on ability score (Dexterity) to 20 to be successful, so there is a lot of room for you to pick up feats if you're willing to deviate from the Basic Rules and the SRD. If you're new to the game, consider simple feats like Skilled or Resilient. If you want to dabble in magic, consider Magic Initiate and take a look at the Spells section above.

Levels

Level Feat(s) and Features Notes and Tactics
1
  • Expertise
    • Perception
    • Stealth
  • Sneak Attack 1d6
  • Thieves' Cant

For your starting equipment, take a shortsword, a short bow, any of the pack options, leather armor, two daggers, and theives' tools.

At first level you already have most of what makes you a decent rogue. Sneak Attack is still picking up steam, but 1d6 is a big chunk of damage at this level, so do everything you can to get it.

In combat, you can either fight at range or jump into melee as the situation warrants. If you're fighting at range, you're totally dependent on an ally to be adjacent to your target, so make sure to communicate with your party's front-line characters. If you're fighting in melee, grab your short sword and a dagger and practice two-weapon fighting. If an enemy is just out of reach, throw your dagger; you have two for a reason.

One Attack: Dagger 1d4+3 with +1d6 Sneak Attack (DPR 5.6)

Two-Weapon Fighting: Dagger 1d4+3 and Dagger 1d4 with +1d6 Sneak Attack (DPR 8.1)

2
  • Cunning Action

Cunning Action shakes up your action economy in combat. Now you need think a little more about how to use your Bonus Action.

If you're fighting at range, find cover (potentially behind a medium-sized ally) to hide behind. Each turn you should attack with your bow then use Cunning Action to hide.

If you're fighting in melee, hit-and-run tactics are the ideal. Attack with your short sword, then use Cunning Action to Disengage and move away safely. If you miss, consider using your bonus action to attack with your dagger to get a second chance at dealing Sneak Attack. If you hit and kill your target, consider using Cunning Action to Dash and put some extra distance between you and anything dangerous.

One Attack: Dagger 1d4+3 with +1d6 Sneak Attack (DPR 5.6)

Two-Weapon Fighting: Dagger 1d4+3 and Dagger 1d4 with +1d6 Sneak Attack (DPR 8.1)

3
  • Sneak Attack 2d6
  • Roguish Archetype (Thief)
  • Fast Hands

At 2d6, yor Sneak Attack damge should roughly match the total damage from your weapons and your Dexterity bonus.

Fast Hands is easy to overlook, but the "Use an Item" action covers a lot of great options. Ball Bearings, Caltrops, Holy Water, potions, and some magic items are all activated as an action normally. You can do all of those things as a Bonus Action, so you could attack, throw down some caltrops, then move to safety all in one turn.

One Attack: Dagger 1d4+3 with +2d6 Sneak Attack (DPR 7.8)

Two-Weapon Fighting: Dagger 1d4+3 and Dagger 1d4 with +2d6 Sneak Attack (DPR 11.2)

4
  • Ability Score Improvement (Dexterity 16 -> 18)

A numerical increase to the vast majority of what you do feels very satisfying.

One Attack: Dagger 1d4+4 with +2d6 Sneak Attack (DPR 8.4)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +2d6 Sneak Attack (DPR 11.8)

5
  • Sneak Attack 3d6
  • Uncanny Dodge

More Sneak Attack damage is always welcome, but it doesn't change our tactics in any way. Uncanny Dodge is the interesting gain here. Since it uses your Reaction, it won't cut into your normal activity during your turn. In some cases you might risk provoking an Opportunity Attack knowing that you can use Uncanny Dodge to reduce the damage if you get hit. If you decide to stay still, you can mitigate some damage with Uncanny Dodge but remember that you only get one Reaction per round so creatures with multiple attacks may be a problem.

One Attack: Dagger 1d4+4 with +3d6 Sneak Attack (DPR 10.6)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +3d6 Sneak Attack (DPR 14.9)

6
  • Expertise
    • Sleight of Hand
    • Thieves' Tools

Fast Fingers allows you to perform Sleight of Hand checks and to use your Thieves' Tools for certain tasks as a bonus action. Expertise will make you better at these tasks. I'm not entirely sure under what circumstances you would do this, but you're now really good at picking pockets in the middle of a fight.

One Attack: Dagger 1d4+4 with +3d6 Sneak Attack (DPR 10.6)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +3d6 Sneak Attack (DPR 14.9)

7
  • Sneak Attack 4d6
  • Evasion

Evasion makes many AOE effects, including breath weapons and fireballs, less threatening. Your Dexterity saves should be excellent, so you'll frequently be able to fully avoid damage from applicable effects.

One Attack: Dagger 1d4+4 with +4d6 Sneak Attack (DPR 12.8)

Two-Weapon Fighting: Dagger 1d4+4 and Dagger 1d4 with +4d6 Sneak Attack (DPR 18.0)

8
  • Ability Score Improvement (Dexterity 18 -> 20)

This brings our Dexterity to the maximum.

One Attack: Dagger 1d4+5 with +4d6 Sneak Attack (DPR 13.4)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +4d6 Sneak Attack (DPR 18.6)

9
  • Sneak Attack 5d6
  • Supreme Sneak

Between Expertise and your 20 Dexterity, you have a +13 bonus on Dexterity (Stealth) checks, and now you have a way to get Advantage guaranteed. You're borderline undetectable.

One Attack: Dagger 1d4+5 with +5d6 Sneak Attack (DPR 15.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +5d6 Sneak Attack (DPR 21.7)

10
  • Ability Score Improvement (Charisma 14 -> 16)

At this level we're getting an Ability Score Increase that we don't strictly need. I've suggested Charisma, but if you're doing more fighting than talking you may want Constitution instead.

One Attack: Dagger 1d4+5 with +5d6 Sneak Attack (DPR 15.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +5d6 Sneak Attack (DPR 21.7)

11
  • Sneak Attack 6d6
  • Reliable Talent

Reliable Talent makes you really good at skills. You're already really good, but this removes the possibility of horribly low rolls. It raises the average d20 roll from 10.5 to 12.75, and a +2.25 bonus on all your skills is huge.

One Attack: Dagger 1d4+5 with +6d6 Sneak Attack (DPR 17.9)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +6d6 Sneak Attack (DPR 24.9)

12
  • Ability Score Improvement (Charisma 16 -> 18)

More Constitution or Charisma. Or a feat. Your choice.

One Attack: Dagger 1d4+5 with +6d6 Sneak Attack (DPR 17.9)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +6d6 Sneak Attack (DPR 24.9)

13
  • Sneak Attack 7d6
  • Use Magic Device

Use Magic Device only matters in campaigns with magic items, which is odd because 5e so rarely assumes that you use magic items. There are very few magic items with restrictions which this will bypass, but you're going to feel really special if you find one and get to break the rules to use it.

One Attack: Dagger 1d4+5 with +7d6 Sneak Attack (DPR 20.1)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +7d6 Sneak Attack (DPR 27.9)

14
  • Blindsense

Invisibility becomes more common at high levels, and unless you have a spellcaster handy it's often very difficult to deal with. This helps quite a bit, but remember tha you'll still have Disadvantage to attack the creature because you can't see it.

One Attack: Dagger 1d4+5 with +7d6 Sneak Attack (DPR 20.1)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +7d6 Sneak Attack (DPR 27.9)

15
  • Sneak Attack 8d6
  • Slippery Mind

More saving throw proficiencies is always excellent.

One Attack: Dagger 1d4+5 with +8d6 Sneak Attack (DPR 22.3)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +8d6 Sneak Attack (DPR 30.9)

16
  • Ability Score Improvement (Charisma 18 -> 20)

Still more Constitution or Charisma.

One Attack: Dagger 1d4+5 with +8d6 Sneak Attack (DPR 22.3)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +8d6 Sneak Attack (DPR 30.9)

17
  • Sneak Attack 9d6
  • Thief's Reflexes

Two turns in the first round of combat means two opportunities to deal a Sneak Attack early in the fight. Target foes which you can eliminate quickly so that your party starts the fight with an early advantage.

One Attack: Dagger 1d4+5 with +9d6 Sneak Attack (DPR 24.5)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +9d6 Sneak Attack (DPR 34.0)

18
  • Elusive

Short of Pack Tactics, most enemies don't have easy ways to gain Advantage against players, so this won't matter frequently, but the few times it comes up you'll be glad to have it.

One Attack: Dagger 1d4+5 with +9d6 Sneak Attack (DPR 24.5)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +9d6 Sneak Attack (DPR 34.0)

19
  • Sneak Attack 10d6
  • Ability Score Improvement (Constitution 14 -> 16)

More damage, more ability scores.

One Attack: Dagger 1d4+5 with +10d6 Sneak Attack (DPR 26.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +10d6 Sneak Attack (DPR 37.1)

20
  • Stroke of Luck

Stroke of Luck doesn't apply to saving throws, so there's little reason to sit on it. Use it early, use it often.

One Attack: Dagger 1d4+5 with +10d6 Sneak Attack (DPR 26.7)

Two-Weapon Fighting: Dagger 1d4+5 and Dagger 1d4 with +10d6 Sneak Attack (DPR 37.1)